Olefin-diolefin copolymers and mercaptan adducts



Patented Jan. 1, 1952 UNI TED STATES PATENT OFF I CE lOLEFIN-VDIOLEFIN COPOLYMERS AND MERCAPTAN ADDUCTS i John D. Garber, New York, .N. Y., and William I O. Hollyday, Jr Roselle, N. J., assignors to Standard OilIDevelopment Co pany,.a corporation of Delaware No Drawing. Application January 2, 1948, Serial No. 364

placed such heavy service demands thereon that on the order of 5 ,00'0l5,000 Staudinger. These cold have in large measure been overcome by solution of the copolymer in approximately twice carbon lubricants of improved pour and viscosity mercaptan additives are usually added to the impart the improving characteristics. The proportions usually run between about 0.05 to 5% by weight.

appear more clearly from the detailed description maintain gentle refluxing. The reaction temperature may range from about 25 to about +50 F., preferably 32 to 45 F. The polymer was pre- 10 to carbon atoms, e. g. decene and higher 35 ticularly eifective as additives for improving pour 40 her of a condensed with several mercap' decene,- octadecene, polypropylenes, triisobutylene, tetraisobutylene, etc. Suitable diolefins are u e o reaction w held to a t for butadiene, isoprene, 2,3-dimethyl butadiene, about 70 hours. The resulting materials were piperylene, and cyclopentadiene. Amongst the tested in Barosa-v43 and Baton Rouge 442 neutral preferred mercaptans are mercaptans containing +35% Pennsylvania Bright Stock test oils which 10 to 16 aliphatic carbon atoms per molecule dehave ASTM pour points of +5 and +30 F'., rerived from Lorol alcohol, a mixture of alcohols spectively, with the following results:

ASTM pour points, F.

Baton Rouge 442 neutral Hams +3.5% Pennsylvania B. Per Cent Additive 1 Additive:

Butadiene-Octadecene Copolymer --20 Butadrene-Octadecene Copolymer, Cn-Gu Alihatic merceptan from lauryl alcohol adduct. --lb Butadiene-O ctadecene Copolymer, 'letrodecyl mercaptan adduct -25 Butadrene-Octadecene Copolymer, Hexadecyl mercaptan ad -30 Butadiene-Octadecene Copolymer, 50-50 mixture of C14, C10 mercapten adducts -30 The foregoing description contains a limited about one part by weight of butadiene with an number of embodiments of the present invention. excess of tetradecyl mercapta said copolymer It will be understood, however; that many variabeing formed by subjecting the octadecene and tions are possible without departing from the the butadiene to a temperature within a range of spirit and scope of the invention as defined in the 32 F. to 45 F. in the presence of a Friedel-Crafts following claims. catalyst.

JCSHN D'. GARBER. 1. A product consisting essentially of an oil WILLIA C. HOLLYDAY, JR-

soluble condensation product of a copolymer of about two parts by weight oi octadecene and 25 REFERENCES ED 7 about one Part by Weight of butadiene condensed The following references are of record in the with an excess of tetradecyl mercaptan, said 00- m of t t polymer being formed by subjecting the octadecene and the butadiene to a temperature within UNITED STATES T a range of from 32 F. to 45 F. in the presence 30 Number 7 N me Date of a Friedel-Crafts catalyst. 5 0 Allen Aug. 25, 1936 2. A lubricating composition comprising a 3 R b- 1941 major proportion of a mineral lubricating oil and 2,346,153 De n o a1 p 1944 a minor but pour depressing amount of an oil 2,352,435 Hoefielman et June 9 soluble condensation prod ct of a copolymer of 35 6 53 Meadow Jan. 2, 1945 about two parts by weight of octadecene and 2,431,257 i' pt 6, 49 

1. A PRODUCT CONSISTING ESSENTIALLY OF AN OIL SOLUBLE CONDENSATION PRODUCT OF A COPOLYMER OF ABOUT TWO PARTS BY WEIGHT OF OCTADECENE AND ABOUT ONE PART BY WEIGHT OF BUTADIENE CONDENSED WITH AN EXCESS OF TETRADECYL MERCAPTAN, SAID COPOLYMER BEING FORMED BY SUBJECTING THE OCTADECENE AND THE BUTADIENE TO A TEMPERATURE WITHIN A RANGE OF FROM 32* F. TO 45* F. IN THE PRESENCE OF A FRIEDEL-CRAFT CATALYST. 